Process for imparting a coumarin-like aroma and flavor to tobacco, foods and drinks

Abstract

A coumarin-like aroma and flavor is imparted to tobacco, foods and drinks by adding the 2- and/or 3-alkyl-substituted indanone compound, such as, 3,4-dimethyl-7-methoxyindan-1-one and 2,4-dimethyl-7-ethoxyindan-1-one. Such a aroma and flavor is further imparted by adding an aromatic composition comprizing said indanone compound, heliotropin and the alkyllactone, such as γ-hexalactone and β,δ-dimethyl-δ-valerolactone. The favourable examples of foods and drinks in this process are oil and fat product such as margarin and shortening; dairy product such as butter, cheese and yoghurt; meat product such as ham, sausage and bacon; confectionary such as cake and candy, fermentation product such as wine and brandy; drink such as cocoa, coffee, cocacola and soft drinks.

What we claim is: 
     
       1. Process for imparting a coumarin-like aroma and flavor to a consumable product selected from the group consisting of tobacco, food and drink, which comprises adding to said product at least one 2- and/or 3-alkyl-substituted indanone compound having the general structural formula: ##SPC4## where either each of R 1  and R 2  represents CH 3  --, C 2  H 5  --, (CH 3 ) 2  CH--, HO--, CH 3  O-- or C 2  H 5  O--, or R 1  combined with R 2  represents --O--CH 2  --O--; and each of R 3  and R 4  represents H, CH 3 , C 2  H 5 , n--C 3  H 7  or (CH 3 ) 2  CH--, excepting the case when both of R 3  and R 4  represent H.   
     
     
       2. Process as claimed in claim 1, wherein the 2- and/or 3-alkyl-substituted indanone compound [I] is at least one member selected from the group consisting of 3,4-dimethyl-7-hydroxyindan-1-one, 3,4-dimethyl-7-methoxyindan-1-one, 3,4-dimethyl-7-ethoxyindan-1-one, 2,4-dimethyl-7-ethoxyindan-1-one, 2-isopropyl-4-methyl-7-hydroxyindan-1-one, 3-isopropyl-4-methyl-7-hydroxyindan-1-one, 3,4,7-trimethylindan1-one, 2-ethyl-4,7-dimethylindan-1-one, 3-isopropyl-4,7-dimethylindan-1-one, 2-methyl-4-, 7-dimethoxyindan-1-one, 3-methyl-4, 7-dimethoxyindan-1-one, 2-isopropyl-4,7-dimethoxyindan-1-one, 3-isopropyl-4,7-dimethoxyindan-1-one,3-methyl-4,7diethoxyindan-1-one, 3-isopropyl-4,7-diethoxyindan-1-one, 2-methyl-5,6-methylenedioxindan-1-one, 3-methyl-5,6-methylenedioxyindan-1-one, 3-ethyl-5,6-methylenedioxyindan-1-one, 3-isopropyl-5,6-methylenedioxyndan-1-one, 2-methyl-4-methoxy-7-hydroxyindan-1-one and 3-isopropyl-4-methoxy-7-hydroxyindan-1-one. 
     
     
       3. Process as claimed in claim 1, wherein the 2- and/or 3-alkyl-substituted indanone compound [I] is added to consumable product in an amount of about 1 to about 100 ppm by weight of said product. 
     
     
       4. Process as claimed in claim 1, wherein the2- and/or 3-alkyl-substituted indanone compound [I] is dissolved in at least one solvent selected from the group consisting of propylene glycol, aqueous glycerol solution and ethanol. 
     
     
       5. Process as claimed in claim 1, wherein at least one modifier selected from the group consisting of ethyl vanillin, methyl anthranylate, eugenol, isoeugenol and cinnamic aldehyde, is used together with the said indanone compound [I]. 
     
     
       6. Process as claimed in claim 1, wherein the consumable product is selected from the group consisting of margarin, shortening, butter, cheese, yoghurt, ham, sausage, bacon, cake, candy, wine, brandy, cocoa, coffee, and soft drinks. 
     
     
       7. Process as claimed in claim 1, wherein the 2- and/or 3-alkyl-substituted indanone compound [I] is applied to at least one product selected from shredded tobacco, re-constituted tobacco, pipe tobacco and/or cigar tobacco. 
     
     
       8. Process as claimed in claim 1, wherein to said consumable product are added together with the said 2- and/or 3-alkyl-substituted indanone compound [I], heliotropin and alkyllactone expressed either by the general structural formula: ##EQU4## wherein each of R, R', R" and R'" shows H, CH 3 , C 2  H 5 , C 3  H 7 , C 4  H 9 , C 5  H 11 , C 6  H 13 , or --(CH 2 ) 2  CH=CHC 2  H 5 , or by the general structural formula: ##EQU5## where each of R, R', R" and R'" shows H, CH 3 , C 2  H 5 , C 3  H 7 , C 4  H 9 , --CH 2  OCH 3  or --CH 2  OC 2  H 5 . 
     
     
       9. Process as claimed in claim 8, wherein the 2- and/or 3-alkyl-substituted indanone compound [I] comprises at least one member selected from the group consisting of 3,4-dimethyl-7-hydroxyindan-1-one, 3,4-dimethyl-7-methoxyindan1-one, 3,4-dimethyl-7-ethoxyindan-1-one, 2,4,-dimethyl-7-ethoxyindan-1-one, 2-isopropyl-4-methyl-7-hydroxyindan-1-one, 3-isopropyl-4-methyl-7-hydroxyindan-1-one, 3,4,7-trimethylindan-1-one, 2-ethyl-4,7-dimethylindan-1-one, 3-isopropyl-4,7-dimethylindan-1-one, 2-methyl-4,7-dimethoxyindan-1-one, 3-methyl-4, 7-dimethoxyindan-1-one, 2-isopropyl-4,7-dimethoxyindan-1-one, 3-isopropyl-4,7-dimethoxyindan-1-one, 3-methyl-4,7-diethoxyindan-1-one, 3-isopropyl-4,7-diethoxyindan-1-one, 2-methyl-5,6-methylenedioxindan-1-one, 3-methyl-5,6-methylenedioxyndan-1-one, 3-ethyl-5,6-methylenedioxyindan-1-one, 3-isopropyl-5,6-methylenedioxyindan-1-one, 2-methyl-4-methoxy-7-hydroxyindan-1-one and 3-isopropyl-4-methoxy-7-hydroxyindan-1-one. 
     
     
       10. Process as claimed in claim 8, wherein said akyllactone [II] or [III] comprises at least one member selected from the group consisting of γ hexalactone, γ-heptalactone, γ-octalactone, α-ethyl-γ-methyl-γ-butyrolactone, α, γ-diethyl-γ-butyroloactone, γ-methyl-γ-ethyl-γ-butyrolactone, γ-methyl-γ-isopropyl-γ-butyrolactone, γ-methyl-γ-n-hexyl-γ-butyrolactone, γ-methyl-γ-hexenyl-γ-butyrolactone, α, β, γ-trimethyl-γ-butyrolactone, α-isopropyl-β-methyl-γ-methyl-γ-butyrolactone, γ-methyl-δ-valerolactone, δ-methyl-δ-valerolactone δ-nonaclactone, δ-decalactone, δ-undecalactone, β,δ-dimethyl-δ-valerolactone, β,β,δ-trimethyl-δ-ethyl-δ-valerolactone, α,γ-dimethyl-γ-methoxymethyl-δ-valerolactone and α,γ-dimethyl-γ-ethoxymethyl-δ-valerolactone. 
     
     
       11. Process as claimed in claim 8, wherein the indanone compound [I] is dissolved in at least one solvent selected from the group consisting of ethyl vanillin, methyl anthranylate eugenol, isoeugenol and cinnamic aldehyde, and said solvent is used together with the said indanone compound [I]. 
     
     
       12. Process as claimed in claim 8, wherein the proportions of the ingredients added together are as follows:   Indanone compounds (1)                                                    
                     0.5-2.0    part                                      
Heliotropin          0.3-0.7    part                                      
Alkyllactone         0.5-1.2    part                                      
Other aromatics (modifier)                                                
                     below 0.1  part                                      
Solvent              6-10       part                                      
     and the proportions of the indanone compound [I] is 20-60% of the amount of all the other constituents except the solvent.   
     
     
       13. Process as claimed in claim 1, wherein the said indanone compound [I] is added to the consumable product in an amount of about 0.1-10 ppm by weight of said product. 
     
     
       14. Process as claimed in claim 8, wherein said consumable product comprises one member selected from the group consisting of margarin, shortening, butter, cheese, yoghurt, ham, sausage, bacon, cake, candy, wine, brandy, cocoa, coffee, and soft drinks. 
     
     
       15. Process as claimed in claim 8, wherein the said indanone compound [I] is applied to shredded tobacco, re-constituted tobacco, pipe tobacco or cigar tobacco.